Patent GB-813188-A (GB)
Title: Improvements in epoxide products e.g. resins
IPC: C08G59/00
Filed: 1956-06-22
Abstract: Epoxide resins are produced by reacting a mixture of cyanuric acid and a dihydric phenol with epichlorhydrin in the presence of an organic nitrogen catalyst and an organic solvent for the reactants and products and subjecting the resulting chlorhydrin derivatives to dehydrohalogenation to form epoxide resins.  Using a large excess of epichlorhydrin which may also serve as the organic solvent products of low molecular weight which are largely monomeric may be obtained. With lower proportions of epichlorhydrin and an inert solvent resinous products are produced.  Suitable catalysts are tertiary amines, e.g. tripropyl amine, dimethyl aniline, quaternary ammonium hydroxides or salts, e.g. benzyl trimethyl ammonium hydroxide or chloride, and quaternary ammonium ion-exchange resins. Dehydrohalogenation is effected with basic reagents, e.g. sodium, potassium or calcium hydroxide or sodium carbonate.  Liquid or low melting products may be reacted with further dihydric phenol or cyanuric acid to produce high melting resins.  In the examples: (1) a mixture of 2,21-bis-(p-hydroxyphenyl) propane, cyanuric acid, an excess of epichlorhydrin and benzyltrimethyl ammonium chloride was heated to 100 DEG  C. until all the cyanuric acid had dissolved. Flake sodium hydroxide was added after cooling and water and epichlorhydrin removed by vacuum distillation.  Salt and unreacted alkali were removed by filtration.  A viscous liquid product was obtained.  Examples (2)-(5) were similar with varying proportions of dihydric phenol to cyanuric acid.  Example (6) uses resorcinol as the dihydric phenol, and Example (7) p.p1-dihydroxydiphenylsulphone.  The liquid products of these examples can be used with a catalyst, e.g. an amine as adhesives, or casting or coating compositions.  The remaining examples use less epichlorhydrin, an inert solvent, e.g. dioxane as reaction medium and produce solid resinous products which may be used for moulding, or in solution as coating compositions. Reference has been directed by the Comptroller to Specification 755,468.ALSO:Monomeric compounds containing epoxy groups are produced by reacting a mixture of cyanuric acid and a dihydric phenol with a large excess of epichlorhydrin in the presence of an organic nitrogen catalyst and subjecting the resulting chlorhydrin derivatives to dehydrochlorination.  Suitable catalysts are tertiary amines, e.g. tripropylamine, dimethyl aniline, quaternary ammonium hydroxides or salts, e.g. benzyl trimethyl ammonium hydroxide or chloride and quaternary ammonium ion-exchange resins.  Dehydrohalogenation is effected with basic reagents, e.g. sodium, potassium or calcium hydroxide or sodium carbonate.  In Example (1) a mixture of 2,21 - bis - (p - hydroxyphenyl) propane, cyanuric acid, an excess of epichlorhydrin and benzyltrimethyl ammonium chloride was heated to 100 DEG  C. until all the cyanuric acid had dissolved.  Flake sodium hydroxide was added after cooling and water and epichlorhydrin removed by vacuum distillation.  Salt and unreacted alkali were filtered off leaving a viscous liquid product.  Examples (2)-(5) are similar with varying proportions of dihydric phenol to cyanuric acid. Example (6) uses resorcinol as the dihydric phenol; and Example (7), p,p1-dihydroxydiphenylsulphone.  Reference has been directed by the Comptroller to Specification 755,468.